KR20210112425A - Organic electroluminescence device and organometallic compound for organic electroluminescence device - Google Patents

Abstract

An organic electroluminescence element of one embodiment includes a first electrode, a second electrode disposed on the first electrode, and a light emitting layer disposed between the first electrode and the second electrode. The light emitting layer may include an organometallic compound represented by the following chemical formula 1 to exhibit high luminous efficiency characteristics.

Description

Organic electroluminescent device and organometallic compound for organic electroluminescent device

The present invention relates to an organic electroluminescent device and an organometallic compound used therefor.

Recently, as an image display device, an organic electroluminescence display has been actively developed. An organic electroluminescent display device is different from a liquid crystal display device, and by recombination of holes and electrons injected from the first and second electrodes in the light emitting layer, the light emitting material containing the organic compound is emitted in the light emitting layer to realize display. It is a so-called self-luminous type display device.

In applying the organic electroluminescent device to a display device, low driving voltage, high luminous efficiency, and long life of the organic electroluminescent device are required, and the development of a material for an organic electroluminescent device that can stably implement this is continuously required. have.

On the other hand, although development of an organometallic compound used as a dopant material in the development of a light emitting layer material continues, development of a dopant material exhibiting high efficiency in a blue light emitting region is still required.

An object of the present invention is to provide an organometallic compound having excellent luminous efficiency and long life characteristics.

Another object of the present invention is to provide an organic electroluminescent device having high efficiency and long lifespan by including an organometallic compound in a light emitting layer.

One embodiment is a first electrode; a second electrode disposed on the first electrode; and a light emitting layer disposed between the first electrode and the second electrode. Including, wherein the light emitting layer provides an organic electroluminescent device comprising an organometallic compound represented by the following formula (1).

[Formula 1]

In Formula 1, M is a transition metal, _{one or two selected from X 1} to X ₆ is N, the rest is CR ₄ , and when X ₁ is N, any one of _{X 2} to X _{6 is N,} R ₄ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group _{having 1} to 10 carbon atoms, A 1 to A ₃ are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 1 or more and 60 or less ring carbon atoms, b1 to b3 are each independently an integer of 1 or more and 4 or less, and R ₁ to R ₃ are each independently a hydrogen atom, a deuterium atom, or a halogen atom. , hydroxyl group, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted oxy group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted ring carbon number 1 and 10 or less heterocyclic groups, and _{at least one of R 1} to R ₃ is a deuterium atom or CD ₃ , or at least one of _{R 1} to R _{3 is substituted with a deuterium atom or CD 3} , and L is a direct bond, O, S, —CR ₁₁ R ₁₂ —, —CR ₁₃ =CR ₁₄ —, —C≡C—, —C(=O)—, —C(=S)—, —BR ₁₅ —, —NR ₁₆ — , —PR ₁₇ R ₁₈ —, or —GeR ₁₉ R ₂₀ —, and R ₁₁ to R ₂₀ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or an unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms.

M may be Pt, Pd, Cu, or Os.

The light emitting layer may emit phosphorescence.

The emission layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1 above.

Formula 1 may be represented by Formula 2-1 or Formula 2-2 below.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, A ₁ to A ₃ , X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b ₃ are the same as defined in Formula 1 above.

Formula 1 may be represented by Formula 3 below.

[Formula 3]

In Formula 3, R ₅₀ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and M, L, X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b ₃ are the same as defined in Formula 1 above.

Formula 3 may be represented by Formula 3-1 below.

[Formula 3-1]

In Formula 3-1, _{any one of X 2} to X ₆ is N, the rest is CR ₄ , M, L, R ₁ to R ₄ , R ₅₀ and b ₁ to b ₃ are as defined in Formula 3 same.

Formula 3 may be represented by Formula 3-1 below.

[Formula 3-1]

In Formula 3-1, _{any one of X 2} to X ₆ is N, the rest is CR ₄ , M, L, R ₁ to R ₄ , R ₅₀ and b ₁ to b ₃ are as defined in Formula 3 same.

Formula 3 may be represented by Formula 3-2 or Formula 3-3.

[Formula 3-2]

[Formula 3-3]

In Formula 3-2, _{any one of X 2} to X ₄ is N, the rest is CR ₄ , R ₅ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 or more and 10 or less carbon atoms, In Formula 3-3, _{any one of X 5} and X ₆ is N, the rest is CR ₆ , b4 is an integer of 1 or more and 4 or less, and R ₆ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted It is an alkyl group having 1 or more and 10 or less carbon atoms, and M, L, R ₁ to R ₄ , b ₁ to b ₃ , and R ₅₀ are the same as defined in Formula 3 above.

R ₅₀ may be represented by any one of the compounds of the following compound group R.

[Compound group R]

.

.

When R ₅₀ is the compound R-7 or R-8, R ₁ may include at least one deuterium atom.

One embodiment provides an organometallic compound represented by Formula 1 above.

The organometallic compound of an embodiment may include a carboline group and a deuterium atom to contribute to high efficiency and long lifespan characteristics of the organic electroluminescent device.

The organic electroluminescent device of an exemplary embodiment may include an organometallic compound including a carboline group and a deuterium atom to exhibit high efficiency and long lifespan device characteristics.

1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present invention.
3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.
4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.

Since the present invention can have various changes and can have various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to the specific disclosed form, it should be understood to include all modifications, equivalents and substitutes included in the spirit and scope of the present invention.

In this specification, when a component (or region, layer, part, etc.) is referred to as being “on,” “connected to,” or “coupled to” another component, it is directly disposed/on the other component. It means that it can be connected/coupled or a third component can be placed between them.

Like reference numerals refer to like elements. In addition, in the drawings, thicknesses, ratios, and dimensions of components are exaggerated for effective description of technical content.

“and/or” includes any combination of one or more that the associated configurations may define.

Terms such as first, second, etc. may be used to describe various elements, but the elements should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, a first component may be referred to as a second component, and similarly, a second component may also be referred to as a first component. The singular expression includes the plural expression unless the context clearly dictates otherwise.

In addition, terms such as "below", "below", "above", "upper" and the like are used to describe the relationship between the components shown in the drawings. The above terms are relative concepts, and are described based on directions indicated in the drawings.

Unless defined otherwise, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Also, terms such as terms defined in commonly used dictionaries should be construed as having a meaning consistent with their meaning in the context of the relevant art, and unless they are interpreted in an ideal or overly formal sense, they are explicitly defined herein do.

Terms such as “comprise” or “have” are intended to designate that a feature, number, step, action, component, part, or combination thereof described in the specification is present, and includes one or more other features, numbers, or steps. , it should be understood that it does not preclude the possibility of the existence or addition of , operation, components, parts, or combinations thereof.

Hereinafter, an organic electroluminescent device according to an embodiment of the present invention and an organometallic compound included therein according to an embodiment will be described with reference to the drawings.

1 to 4 are cross-sectional views schematically illustrating an organic electroluminescent device according to an embodiment of the present invention. 1 to 4 , in the organic electroluminescent device 10 according to an embodiment, the first electrode EL1 and the second electrode EL2 are disposed to face each other, and the first electrode EL1 and the second electrode An emission layer EML may be disposed between the EL2 .

In addition, the organic electroluminescent device 10 according to an embodiment further includes a plurality of functional layers in addition to the light emitting layer EML between the first electrode EL1 and the second electrode EL2. The plurality of functional layers may include a hole transport region (HTR) and an electron transport region (ETR). That is, the organic electroluminescent device 10 according to an embodiment has a first electrode EL1, a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and a second electrode ( EL2) may be included. In addition, the organic electroluminescent device 10 according to an exemplary embodiment may include a capping layer CPL disposed on the second electrode EL2 .

The organic electroluminescent device 10 of an embodiment may include the organometallic compound of an embodiment to be described later in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2.

Meanwhile, in FIG. 2 , compared with FIG. 1 , the hole transport region HTR includes the hole injection layer HIL and the hole transport layer HTL, and the electron transport region ETR includes the electron injection layer EIL and the electron transport layer. A cross-sectional view of the organic electroluminescent device 10 of an embodiment including (ETL) is shown. In addition, in FIG. 3 , the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL) as compared with FIG. 1 , and the electron transport region (ETR) is an electron injection region A cross-sectional view of an organic electroluminescent device 10 including a layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL) is shown. 4 is a cross-sectional view of the organic electroluminescent device 10 according to an embodiment including the capping layer CPL disposed on the second electrode EL2 as compared with FIG. 2 .

The first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal alloy or a conductive compound. The first electrode EL1 may be an anode. Also, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium (ITZO). tin zinc oxide) and the like. When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg). Or a plurality of layer structures including a reflective or semi-transmissive film formed of the above material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. can be For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. The thickness of the first electrode EL1 may be about 1000 Å to about 10000 Å, for example, about 1000 Å to about 3000 Å.

The hole transport region HTR is provided on the first electrode EL1 . The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 50 Å to about 15000 Å.

The hole transport region HTR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure including a hole injection material and a hole transport material. In addition, the hole transport region HTR has a single layer structure made of a plurality of different materials, or a hole injection layer HIL/hole transport layer HTL, hole injection that are sequentially stacked from the first electrode EL1 . Layer (HIL) / hole transport layer (HTL) / hole buffer layer (not shown), hole injection layer (HIL) / hole buffer layer (not shown), hole transport layer (HTL) / hole buffer layer or hole injection layer (HIL) / hole transport layer (HTL)/electron blocking layer (EBL) may have a structure, but the embodiment is not limited thereto.

The hole transport region (HTR) is a vacuum deposition method, a spin coating method, a casting method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser thermal imaging method (Laser Induced Thermal Imaging, LITI), such as various methods It can be formed using

The hole injection layer HIL may include, for example, a phthalocyanine compound such as copper phthalocyanine; DNTPD(N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4' ,4"-[tris(3-methylphenyl)phenylamino] triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris{ N-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA(Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA (Polyaniline/Camphor sulfonicacid), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate)), NPB(N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), triphenylamine Polyether ketone containing (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis (pentafluorophenyl) borate], HAT-CN (dipyrazino [2,3-f: 2',3'-h] quinoxaline-2, 3,6,7,10,11-hexacarbonitrile) and the like.

The hole transport layer (HTL) is, for example, a carbazole-based derivative such as N-phenylcarbazole and polyvinylcarbazole, a fluorene-based derivative, TPD (N,N'-bis(3-methylphenyl)-N, Triphenylamine derivatives such as N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine), NPB(N ,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC(4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4 ,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP(1,3-Bis(N-carbazolyl)benzene), etc. may be further included.

The hole transport region HTR may have a thickness of about 50 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. The thickness of the hole injection layer HIL may be, for example, about 30 Å to about 1000 Å, and the thickness of the hole transport layer HTL may be about 30 Å to about 1000 Å. For example, the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. When the thicknesses of the hole transport region (HTR), the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) satisfy the above-described ranges, satisfactory hole transport characteristics without a substantial increase in driving voltage can get

The hole transport region HTR may further include a charge generating material to improve conductivity, in addition to the aforementioned materials. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane); and metal oxides such as tungsten oxide and molybdenum oxide, but is not limited thereto.

As described above, the hole transport region HTR may further include at least one of a hole buffer layer (not shown) and an electron blocking layer EBL, in addition to the hole injection layer HIL and the hole transport layer HTL. The hole buffer layer (not shown) may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer EML. As a material included in the hole buffer layer (not shown), a material capable of being included in the hole transport region HTR may be used. The electron blocking layer EBL is a layer serving to prevent electron injection from the electron transport region ETR to the hole transport region HTR.

The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have a thickness of, for example, about 100 Å to about 1000 Å, or about 100 Å to about 300 Å. The emission layer EML may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

In the organic electroluminescent device 10 according to an embodiment, the emission layer EML may include an organometallic compound according to an embodiment to be described later.

In the present specification, "substituted or unsubstituted" is a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine group, A phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group and one or more substituents selected from the group consisting of a heterocyclic group may mean unsubstituted or substituted. have. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

In the present specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

In the present specification, the alkyl group may be linear, branched or cyclic. Carbon number of an alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl group Siloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-ox Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-tricho Sil group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, etc. are mentioned, It is not limited to these.

In the present specification, the alkenyl group refers to a hydrocarbon group including one or more carbon double bonds in the middle or terminal of an alkyl group having 2 or more carbon atoms. The alkenyl group may be straight-chain or branched. Although carbon number is not specifically limited, 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the alkenyl group include, but are not limited to, a vinyl group, a 1-butenyl group, a 1-pentenyl group, a 1,3-butadienyl aryl group, a styrenyl group, and a styryl vinyl group.

In the present specification, the alkynyl group refers to a hydrocarbon group including one or more carbon triple bonds in the middle or terminal of an alkyl group having 2 or more carbon atoms. The alkynyl group may be straight chain, branched chain, or cyclic. Although carbon number is not specifically limited, 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Specific examples of the alkynyl group include, but are not limited to, an ethynyl group, a propynyl group, and the like.

In the present specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of ring carbon atoms of the hydrocarbon ring group may be 5 or more and 60 or less, 5 or more and 30 or less, or 5 or more and 20 or less.

As used herein, the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of the aryl group include a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a quinkphenyl group, a sexyphenyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group , a chrysenyl group, and the like can be exemplified, but the present invention is not limited thereto.

As used herein, the heterocyclic group refers to any functional group or substituent derived from a ring including at least one of B, O, N, P, Si and S as a hetero atom. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, the heteroaryl group may include one or more of B, O, N, P, Si and S as a hetero atom. When the heteroaryl group includes two or more hetero atoms, the two or more hetero atoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinoline group, quinazoline group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N -Heteroarylcarbazole group, N-alkylcarbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuran group, phenane Trollin group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilol group and dibenzofuran group, but are not limited thereto.

In the present specification, the silyl group includes an alkyl silyl group and an aryl silyl group. Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. not limited

In the present specification, the oxy group may include an alkoxy group and an aryl oxy group. The alkoxy group may be straight-chain, branched-chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but may be, for example, 1 or more and 20 or less or 1 or more and 10 or less. Examples of the oxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc. it is not

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include an alkyl amine group, an aryl amine group, or a heteroaryl amine group. Examples of the amino group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, and a triphenylamine group.

" 는 연결되는 위치를 의미한다.On the other hand, in this specification "

" means the location to be connected.

The organometallic compound according to an embodiment may be represented by Formula 1 below.

[Formula 1]

In Formula 1, M is a central metal atom, and M is a transition metal.

In Formula 1, _{one or two selected from X 1} to X ₆ is N(Nitrogen), and the remainder is CR ₄ . When one of X ₁ to X ₆ is selected, one of X ₂ to X ₆ may be selected. In the case of selecting the two of X ₁ to X ₆ is or X ₁ is selected and X ₂ to X ₆ is selected from one, two may be selected from X ₂ to X _6. In Formula 1, _{one or two selected from X 1} to X _{6 may} be N (Nitrogen), and the remaining _{aromatic condensed ring having CR 4} may be a carboline group.

When X ₁ is N, at least one of _{X 2} to X _{6 is N.} That is, the case where X ₁ is N and X ₂ to X ₆ is all CR ₄ is excluded. R ₄ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, when X ₁ is N, X ₃ may be N, and X ₂ , X ₄ , X ₅ and X ₆ may be CH.

A ₁ to A ₃ may each independently represent a substituted or unsubstituted hydrocarbon ring having 5 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 1 to 60 carbon atoms. For example, A ₁ and A ₂ may each independently be a heteroaryl group having 5 or more and 10 or less ring carbon atoms, and A ₃ may be an aryl group having 5 or more and 10 or less carbon atoms.

b1 to b3 are each independently an integer of 1 or more and 4 or less. When b1 to b3 are an integer of 2 or more, a plurality of R ₁ to R ₃ may be each independently all the same or at least one different. For example, when b1 is an integer of 2 or more, a plurality of R ₁ may be all the same, or at least one R ₁ may be different from the remaining R _{1 .}

R ₁ to R ₃ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, A substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C6-C6 It may be an aryl group of 60 or more, or a substituted or unsubstituted heterocyclic group having 1 or more and 10 or less ring carbon atoms.

At least one of R ₁ to R ₃ may be a deuterium atom or CD ₃ , or at least one of _{R 1} to R ₃ may be substituted with a _{deuterium atom or CD 3 .} "D" may be a deuterium atom. For example, when b1 is an integer of 2 or more, a plurality of R ₁ may be deuterium atoms. Alternatively, R ₁ may be an aryl group substituted with a deuterium atom.

For example, R ₂ may be a t-butyl group or a methyl group substituted with 3 deuterium atoms. R ₃ may be a hydrogen atom or a t-butyl group. In addition, R ₃ includes a phenyl group substituted with an alkyl group, and the alkyl group may be any one of a methyl group, an isopropyl group, and a methyl group substituted with a deuterium atom. However, this is exemplary, and the embodiment is not limited thereto.

L is a direct linkage, O, S, —CR ₁₁ R ₁₂ —, —CR ₁₃ =CR ₁₄ —, —C≡C—, —C(=O)—, —C(=S)—, —BR ₁₅ —, —NR ₁₆ —, —PR ₁₇ R ₁₈ —, or —GeR ₁₉ R ₂₀ —. For example, L may be an oxygen atom.

R ₁₁ to R ₂₀ may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

_{One or two selected from the group consisting of X 1} to X ₆ of the organometallic compound represented by Chemical Formula 1 is a nitrogen atom, and thus may exhibit an improved MLCT (Metal to Ligand Charge Transfer) ratio. The organometallic compound of an embodiment exhibits a high MLCT ratio, and when used as a light emitting layer material, may contribute to improving the efficiency of an organic electroluminescent device. Meanwhile, the MLCT ratio described herein ^{refers to a triplet metal to ligand charge transfer (MLCT) ratio of 3} , and represents a relative ratio based on 100% charge transfer from a metal atom to a ligand.

In addition, since the organometallic compound according to an exemplary embodiment includes a deuterium atom as a substituent, when used as a material for the light emitting layer, device characteristics with improved lifespan and efficiency may be exhibited.

In Formula 1, M may be a metal atom bonded to a tetracoordinate ligand. M may be a metal atom such as Pt (platinum), Pd (palladium), Cu (copper), or Os (osmium), specifically, M may be Pt.

Meanwhile, Chemical Formula 1 may be represented by the following Chemical Formula 2-1 or Chemical Formula 2-2. Formula 2-1 corresponds to an organometallic compound in which metal atom M is Pt and L is O in Formula 1; Formula 2-2 corresponds to an organometallic compound in which metal atom M in Formula 1 is Pt, and L is —CR ₁₁ R ₁₂ — to R ₁₁ R ₁₂ are all fluorine atoms.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the same contents as those described in Formula 1 may be applied _{to X 1} to X ₆ , R ₁ to R ₃ , and b ₁ to b _{3 .} In addition, Chemical Formula 1 may be represented by Chemical Formula 3 below. Formula 3 shows a case in which A ₁ to A ₃ in Formula 1 is an aromatic ring. A ₁ is imidazole, A ₂ is pyridine, and A ₃ is an aryl group.

[Formula 3]

In Formula 3, R ₅₀ may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

For example, R ₅₀ may include any one of a deuterium atom and an aromatic ring group. R ₅₀ may be a methyl group substituted with a deuterium atom or an aryl group substituted with a deuterium atom. R ₅₀ may be a phenyl group substituted with 1 to 2 isopropyl groups or a phenyl group substituted with 1 to 2 phenyl groups. One or two phenyl groups may include a deuterium atom as a substituent, and all hydrogens of the phenyl group may be substituted with deuterium atoms. However, this is an example, and the embodiment is not limited thereto.

In Formula 3, the same contents as those described in Formula 1 may be applied to M, L, X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b _{3 .}

Chemical formula 3 may be represented by the following Chemical Formula 3-1. In Formula 3, X ₁ to X ₆ represents a case where two selected from N are N.

[Formula 3-1]

In Formula 3-1, X ₁ may be N, _{any one of X 2} to X ₆ may be N, and the rest _{may be CR 4 .} For example, X ₁ and X ₃ may be N, and X ₂ , X ₄ , X ₅ and X ₆ may be CH.

In Formula 3-1, the same contents as those described in Formula 3 may be applied to M, L, R ₁ to R ₄ , R ₅₀ and b ₁ to b _{3 .}

In addition, Chemical Formula 3 may be represented by the following Chemical Formula 3-2 or Chemical Formula 3-3. Unlike Formula 3-1 _{, it represents a case in which one selected from X 1} to X ₆ is N, and in Formulas 3-2 and 3-3, X ₁ is CR ₅ , and any one of _{X 2} to X _{6 is N} and the rest is CR ₄ .

[Formula 3-2]

[Formula 3-3]

In Formula 3-2, _{any one of X 2} to X ₄ may be N, and the rest _{may be CR 4 .} For example, X ₂ may be N, X ₃ and X ₄ may be CR _{4 .} R ₅ may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, R ₄ and R ₅ may be the same as a methyl group.

In Formula 3-3, _{any one of X 5} and X ₆ may be N, and the rest _{may be CR 6 .} R ₆ may be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. b4 may be an integer of 1 or more and 4 or less. For example, X ₅ may be N, X ₆ may be CH, and R ₄ may be a deuterium atom.

In Formulas 3-2 and 3-3, the same contents as those described in Formula 3 may be applied _{to M, L, R 1} to R ₄ , b ₁ to b ₃ , and R _{50 .}

Meanwhile, R ₅₀ may be represented by any one of the compounds of the compound group R.

[Compound group R]

In the compound group R, when R ₅₀ is a compound that does not include a deuterium atom, R ₁ may include a deuterium atom as a substituent. When R ₅₀ is R-7 or R-8, R ₁ may be a deuterium atom. For example, when R ₅₀ is R-7 and b1 is 4, a plurality of R ₁ may all be deuterium atoms.

The organometallic compound of an embodiment may be a light emitting dopant emitting blue light. In addition, the organometallic compound according to an embodiment may be a phosphorescent dopant.

The organometallic compound of an embodiment may be represented by any one of the compounds shown in Compound Group 1 below. The emission layer EML may include at least one of the compounds shown in Compound Group 1 below.

[Compound group 1]

.

.

In the embodiment compounds set forth in compound group 1, "D" corresponds to a deuterium atom.

In the organic electroluminescent device 10 of an embodiment, the light emitting layer (EML) may include an organometallic compound of an embodiment including a carboline group and a deuterium atom to exhibit improved luminous efficiency characteristics. The organometallic compound of one embodiment may exhibit ^{an improved 3} MLCT ratio including a carboline group and a deuterium atom.

On the other hand, in the organic electroluminescent device 10 of an embodiment shown in FIGS. 1 to 4 , the emission layer (EML) may include a host and a dopant, and the emission layer (EML) is an organometallic compound represented by Formula 1 as a dopant. material may be included.

In an embodiment, the emission layer EML may emit phosphorescence. For example, the organometallic compound according to the exemplary embodiment represented by Formula 1 may be a phosphorescent dopant.

Meanwhile, the emission layer EML may further include a host material in addition to the organometallic compound of the above-described exemplary embodiment. In the organic electroluminescent device 10 according to an embodiment, the emission layer EML may include a general material known in the art as a host material. For example, DPEPO(Bis[2-(diphenylphosphino)phenyl]ether oxide), CBP(4,4'-Bis(carbazol-9-yl)biphenyl), mCP(1,3-Bis(carbazol-9-yl) )benzene), PPF (2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine) and TPBi(1, 3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene) may be included. However, it is not limited thereto, and for example, Alq ₃ (tris(8-hydroxyquinolino)aluminum), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK(poly (n-vinylcabazole), ADN(9,10-di(naphthalene-2-yl)anthracene), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1, 3,5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4) ′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN(2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), DPEPO(bis[2-(diphenylphosphino)phenyl) ]ether oxide), CP1(Hexaphenyl cyclotriphosphazene), UGH ₂ (1,4-Bis(triphenylsilyl)benzene), DPSiO ₃ (Hexaphenylcyclotrisiloxane), DPSiO ₄ (Octaphenylcyclotetra siloxane), PPF(2,8-Bis(diphenylphosphoryl)dibenzofuran) , BCPDS(bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane), POPCPA((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide) can

In addition, the light emitting layer (EML) of the organic electroluminescent device 10 according to an embodiment may further include a known dopant material in addition to the above-described organometallic compound. For example, the emission layer EML may further include a known fluorescent dopant material, a known delayed fluorescent dopant material, or a known phosphorescent dopant material.

Meanwhile, although not shown in the drawings, the organic electroluminescent device 10 according to an embodiment may include a plurality of light emitting layers. The plurality of light emitting layers may be sequentially stacked and provided, for example, the organic electroluminescent device 10 including a plurality of light emitting layers may emit white light. The organic electroluminescent device including a plurality of light emitting layers may be an organic electroluminescent device having a tandem structure. When the organic electroluminescent device 10 includes a plurality of emission layers, at least one emission layer EML may include the organometallic compound of an embodiment as described above.

In the organic electroluminescent device 10 of the embodiment shown in FIGS. 1 to 4 , the electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but embodiments are not limited thereto.

The electron transport region ETR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the electron transport region ETR may have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single layer structure including an electron injection material and an electron transport material. In addition, the electron transport region ETR has a single layer structure made of a plurality of different materials, or an electron transport layer (ETL)/electron injection layer (EIL), a hole blocking layer ( HBL)/electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 Å to about 1500 Å.

Electron transport region (ETR), vacuum deposition method, spin coating method, casting method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser thermal imaging (Laser Induced Thermal Imaging, LITI) various methods such as It can be formed using

When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR may include an anthracene-based compound. However, the present invention is not limited thereto, and the electron transport region is, for example, Alq ₃ (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)- 9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7-diphenyl-1 ,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl) -1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq ₂ (berylliumbis(benzoquinolin-10) -olate), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene) and mixtures thereof The thickness of the electron transport layers (ETL) may be from about 100 Å to about 1000 Å, for example, from about 150 Å to about 500 Å. A satisfactory degree of electron transport characteristics can be obtained without increasing the driving voltage.

When the electron transport region ETR includes the electron injection layer EIL, the electron transport region ETR includes a metal halide such as LiF, NaCl, CsF, RbCl, and RbI, a lanthanide metal such as Yb, Li ₂ O, A metal oxide such as BaO or lithium quinolate (Liq) may be used, but is not limited thereto. The electron injection layer EIL may also be formed of a material in which an electron transport material and an insulating organo metal salt are mixed. The organometallic salt may be a material having an energy band gap of about 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. can The electron injection layers EIL may have a thickness of about 1 Å to about 100 Å, and about 3 Å to about 90 Å. When the thickness of the electron injection layers EIL satisfies the above range, a satisfactory level of electron injection characteristics may be obtained without a substantial increase in driving voltage.

As described above, the electron transport region ETR may include the hole blocking layer HBL. The hole blocking layer (HBL) may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). may be included, but is not limited thereto.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium (ITZO). tin zinc oxide) and the like.

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture containing them (eg, a mixture of Ag and Mg). Or a plurality of layer structures including a reflective or semi-transmissive film formed of the above material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. can be

Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

Meanwhile, a capping layer CPL may be further disposed on the second electrode EL2 of the organic electroluminescent device 10 according to an exemplary embodiment. The capping layer (CPL) is, for example, α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra (biphenyl-4-yl) biphenyl-4, 4'-diamine), TCTA (4,4',4"-Tris (carbazol-9-yl) triphenylamine), N, N'-bis (naphthalen-1-yl), etc. may be included.

As described above, the organic electroluminescent device 10 according to an embodiment of the present invention may exhibit excellent luminous efficiency characteristics by including an organometallic compound including a carboline group and a deuterium atom in the light emitting layer (EML).

Hereinafter, an organic metal compound according to an embodiment of the present invention and an organic electroluminescent device according to an embodiment will be described in detail with reference to Examples and Comparative Examples. In addition, the examples shown below are examples for helping understanding of the present invention, and the scope of the present invention is not limited thereto.

[Example]

1. Synthesis of organometallic compounds

The organometallic compound according to an embodiment of the present invention may be synthesized as follows, for example. However, the method for synthesizing the organometallic compound according to an embodiment of the present invention is not limited thereto.

(1) Synthesis of organometallic compound 18

The organometallic compound 18 according to an embodiment may be synthesized, for example, by the step of Scheme 1 below.

[Scheme 1]

(Synthesis of Intermediate A-1)

7-methoxy-9H-pyrido[3,4-b]indole 9.91g (50mmol) and 2-bromo-4-(methyl-d3)pyridine 13.1g (75mmol), potassium triphosphate 23g (100mmol), CuI 1.83 g (10 mmol) and picolinic acid 1.17 g (10 mmol) were placed in a reaction vessel and suspended in 150 mL of dimethyl sulfoxide. The reaction mixture was warmed and stirred at 160° C. for 24 hours. After completion of the reaction, it was cooled to room temperature, 300 mL distilled water was added, and the mixture was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue after removing the solvent was separated using column chromatography to obtain 13.1 g (45 mmol) of the target compound.

(Synthesis of Intermediate A-2)

13.1 g (45 mmol) of intermediate [A-1] was suspended in an excess of hydrobromic acid solution. The reaction mixture was warmed and stirred at 110° C. for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and neutralized by adding an appropriate amount of sodium hydrogen carbonate. 300 mL of distilled water was added, followed by extraction with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue after removing the solvent was separated using column chromatography to obtain 9.56 g (35 mmol) of the target compound.

(Synthesis of Intermediate A-3)

1-(3-bromo-5-t-butyl)phenyl)1H-benzo[d]imidazole 14.2g (43mmol), intermediate [A-2] 9.1g (35mmol), triphosphate potassium 16.2g (70mmol) , CuI 1.3g (7.0mmol), and picolinic acid 0.8g (7.0mmol) were placed in a reaction vessel and suspended in 100 mL of dimethyl sulfoxide. The reaction mixture was warmed and stirred at 160° C. for 24 hours. After completion of the reaction, it was cooled to room temperature, 300 mL distilled water was added, and the mixture was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue after removing the solvent was separated using column chromatography to obtain 13.4 g (26 mmol) of the target compound.

(Synthesis of Intermediate A-4)

13.4 g (26 mmol) of intermediate [A-3] was suspended in an excess of methane iodide. The reaction mixture was warmed and stirred at 110° C. for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was filtered and washed with ether. The washed solid was isolated by recrystallization to obtain 14.8 g (22 mmol) of the target compound.

(Synthesis of Intermediate A-5)

Intermediate [A-4] 14.8 g (22 mmol) and 14.6 g (88 mmol) of ammonium hexafluorophosphate were placed in a reaction vessel, and suspended in a mixed solution of 240 mL of methyl alcohol and 60 mL of water. The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the resulting solid was filtered and washed with ether. The washed solid was dried to give 12.4 g (18 mmol) of the desired compound.

(Synthesis of compound 18)

Intermediate [A-5] 6.2g (9mmol), Dichloro(1,5-cyclooctadiene)platinum 3.7g (9.9mmol), and sodium acetate 4.4g (54mmol) were suspended in 140ml dioxane. The reaction mixture was warmed and stirred at 110 °C for 72 hours. After completion of the reaction, it was cooled to room temperature, 100 ml of distilled water was added, and the mixture was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The solvent was removed and the residue was separated using column chromatography to obtain 1.77 g (2.4 mmol) of the target compound.

(2) Synthesis of organometallic compound 29

Compound 29 according to an embodiment may be synthesized, for example, by the steps of Scheme 2 below.

[Scheme 2]

(Synthesis of Intermediate A-6)

Using the same method as Intermediate A-2 of Synthesis Example 18, except for using 2-bromo-4-(t-butyl)pyridine instead of 2-bromo-4-(methyl-d3)pyridine, The compound was obtained.

(Synthesis of Intermediate A-7)

Use intermediate [A-6] instead of intermediate [A-2] and 1,3-dibromo instead of 1-(3-bromo-5-t-butyl)phenyl) 1H-benzo[d]imidazole The target compound was obtained in the same manner as in Intermediate A-3 of Synthesis Example 18, except that -5-(t-butyl)benzene was used.

(Synthesis of Intermediate A-8)

Intermediate [A-7] 5.28g (10mmol) and N-{[1,1`:3,1"-terphenyl]-2`-yl-d13}benzene-1,2-diamine 3.84 g (11mmol), SPhos (0.75 mmol), Pd ₂ (dba) ₃ (0.5 mmol), and sodium t-butoxide (20 mmol) were suspended in 100 ml of a toluene solvent, heated to 100 ° C., and stirred for 5 hours. After completion of the reaction, the solvent was reduced under reduced pressure. Removed, extracted with methylene chloride and distilled water.The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried over sodium sulfate.The residue after removing the solvent was separated by column chromatography to obtain 6.06g (7.6 mmol) of the target compound. obtained.

(Synthesis of Intermediate A-9)

After dissolving 6.06 g (7.6 mmol) of Intermediate [A-8] 1 mmol in 380 mmol of triethyl orthoformate, 9.12 mmol of HCl is added dropwise. The temperature was raised to 100 °C and stirred for 20 hours. After completion of the reaction, the solvent was removed under reduced pressure, and the mixture was extracted with methylene chloride and distilled water. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue after removing the solvent was separated using column chromatography to obtain 4.98 g (5.9 mmol) of the target compound.

(Synthesis of Intermediate A-10)

The target compound was obtained in the same manner as in Intermediate [A-5] of Synthesis Example 18, except that Intermediate [A-9] was used instead of Intermediate [A-4].

(Synthesis of compound 29)

The target compound was obtained in the same manner as in Synthesis Example 18, except that Intermediate [A-10] was used instead of Intermediate [A-5].

(3) Synthesis of organometallic compound 50

The organometallic compound 50 according to an embodiment may be synthesized, for example, by the steps of Scheme 3 below.

[Scheme 3]

(Synthesis of Intermediate A-11)

The above synthesis except that 7-methoxy-1,3-dimethyl-9H-pyrido[3,4-b]indole is used instead of 7-methoxy-9H-pyrido[3,4-b]indole. The target compound was obtained in the same manner as in Intermediate [A-6] of Example 29.

(Synthesis of Intermediate A-12)

The above synthesis example except that the intermediate [A-11] is used instead of the intermediate [A-6] and the intermediate [B-1] is used instead of the 1,3-dibromo-5-(t-butyl)benzene The target compound was obtained by using the same method as Intermediate [A-7] of 29.

(Synthesis of Intermediate A-13)

Use intermediate [A-12] instead of intermediate [A-7], N-{[1,1`:3,1''-terphenyl]-2`-yl-d13}benzene-1,2-diamine Instead, the target compound was obtained in the same manner as in Intermediate A-8 of Synthesis Example 29, except that Intermediate [B-2] was used.

(Synthesis of Intermediate A-14)

The target compound was obtained in the same manner as in Intermediate [A-9] of Synthesis Example 29, except that Intermediate [A-13] was used instead of Intermediate [A-8].

(Synthesis of Intermediate A-15)

The target compound was obtained in the same manner as in Intermediate [A-10] of Synthesis Example 29, except that Intermediate [A-14] was used instead of Intermediate [A-9].

(Synthesis of compound 50)

An organometallic compound 50 as a target compound was obtained in the same manner as in Synthesis Example 29, except that Intermediate [A-15] was used instead of Intermediate [A-10].

(4) Synthesis of organometallic compound 79

Using 7-methoxy-5H-pyrido[3,4-b]indole instead of 7-methoxy-9H-pyrido[3,4-b]indole, N-{[1,1`:3, 1''-terphenyl]-2`-nyl-d ₁₃ } benzene-1,2-diamine instead of N ¹ -{4`-(methyl-d <sub>3</sub> )-[1,1`[diphenyl]-2- nyl-2`,3`,5`,6`-d ₄ ) The target compound, organometallic compound 79, was obtained in the same manner as in the synthesis of compound 29, except that benzene-1,2-diamine was used. did.

(5) Synthesis of organometallic compound 119

Using 3-methoxy-5H-pyrido [4,3-b] indole-6,7,8,9-d ₄ instead of 7-methoxy-9H-pyrido [3,4-b] indole, N-{[1,1`:3,1''-terphenyl]-2`-yl-d ₁₃ } benzene-1,2-diamine instead of N ¹ -(2,6-di-t-butylphenyl) A target compound, organometallic compound 119, was obtained in the same manner as in the synthesis of compound 29, except that benzene-d _{3 -1,2-diamine was used.}

(6) Synthesis of organometallic compound 129

The organometallic compound 129 according to an embodiment may be synthesized, for example, by the steps of Scheme 4 below.

[Scheme 4]

(Synthesis of Intermediate C-1)

7-bromo-9H-pyrido[3,4-b]indole 12.35g (50mmol) and 2-bromo-4-(t-butyl)pyridine 16.06g (75mmol), trigins potassium 23g (100mmol) ), CuI 1.83 g (10 mmol), and picolinic acid 1.17 g (10 mmol) were placed in a reaction vessel and suspended in 150 mL of dimethyl sulfoxide. The reaction mixture was warmed and stirred at 160° C. for 24 hours. After completion of the reaction, it was cooled to room temperature, 300 mL distilled water was added, and the mixture was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue after removing the solvent was separated using column chromatography to obtain 14.45 g (38 mmol) of the target compound.

(Synthesis of Intermediate C-2)

After dissolving 14.45 g (38 mmol) of the intermediate [C-1] in 500 mL of THF, 41.8 mmol (2.5M in Hexane) of n-butyllithium was slowly added at -78°C. After one hour at 0° C., 10.5 g (57 mmol) of 3-bromobenzaldehyde was added. After stirring for 2 hours, ammonium chloride was added and the mixture was washed 3 times with diethyl ether (30 mL). The washed diethyl ether layer was dried over sodium sulfate. The solvent was removed and the residue was separated using column chromatography to obtain 10.7 g (22 mmol) of the target compound.

(Synthesis of Intermediate C-3)

After 10.7 g (22 mmol) of the intermediate [C-2] was dissolved in dimechloride, 14.9 g (66 mmol) of DDQ was added, followed by stirring at room temperature for 12 hours. After completion of the reaction, it was separated using column chromatography to obtain 8.72 g (18 mmol) of the target compound.

(Synthesis of Intermediate C-4)

After dissolving 8.72 g (18 mmol) of the intermediate [C-3] in dimechloride under nitrogen condition, 18 mL of HF-pyridine was added thereto, followed by stirring at 50° C. for 24 hours. After completion of the reaction, diethyl ether was added to the residue from which the solvent was removed, followed by washing with sodium bicarbonate solution. The washed diethyl ether layer was dried over sodium sulfate. After removing the solvent and stirring the residue under hexane, 8.6 g (17 mmol) of the target compound was obtained through recrystallization.

(Synthesis of Intermediate C-5)

Use intermediate [C-4] instead of intermediate [A-7] and replace N-{[1,1`:3,1”-terphenyl]-2`-yl-d13}benzene-1,2-diamine N ¹ -(2,6-di-t-butylphenyl)benzene-di4-1,2-diamine was prepared using the same method as Intermediate A-8 of Synthesis Example 29, except that the target compound was prepared obtained.

(Synthesis of Intermediate C-6)

A target compound was obtained in the same manner as in Intermediate [A-9] of Synthesis Example 29, except that Intermediate [C-5] was used instead of Intermediate [A-8].

(Synthesis of Intermediate C-7)

A target compound was obtained in the same manner as in Intermediate [A-10] of Synthesis Example 29, except that Intermediate [C-6] was used instead of Intermediate [A-9].

(Synthesis of compound 129)

An organometallic compound 129 as a target compound was obtained in the same manner as in Synthesis Example 29, except that Intermediate [C-7] was used instead of Intermediate [A-10].

(7) Synthesis of organometallic compound 146

The organometallic compound 146 according to an embodiment may be synthesized, for example, by the steps of Scheme 5 below.

[Scheme 5]

(Synthesis of Intermediate C-8)

7-bromo-5H-pyrido [4,3-b] indole instead of 7-bromo-9H-pyrido [3,4-b] indole, 3-bromo-5- ( The target compound was obtained in the same manner as in Intermediate [C-1] of Synthesis Example 129, except that t-butyl)benzaldehyde was used.

(Synthesis of Intermediate C-9)

A target compound was obtained in the same manner as in Intermediate [C-2] of Synthesis Example 129, except that Intermediate [C-8] was used instead of Intermediate [C-1].

(Synthesis of Intermediate C-10)

A target compound was obtained in the same manner as in Intermediate [C-3] of Synthesis Example 129, except that Intermediate [C-9] was used instead of Intermediate [C-2].

(Synthesis of Intermediate C-11)

A target compound was obtained in the same manner as in Intermediate [C-4] of Synthesis Example 129, except that Intermediate [C-10] was used instead of Intermediate [C-3].

(Synthesis of Intermediate C-12)

Use intermediate [C-11] instead of intermediate [A-7] and replace N-{[1,1`:3,1”-terphenyl]-2`-yl-d13}benzene-1,2-diamine A target compound was obtained in the same manner as in Intermediate [A-8] of Synthesis Example 29, except that N ^{1 -(phenyl-di5)benzene-1,2-diamine was used.}

(Synthesis of Intermediate C-13)

A target compound was obtained in the same manner as in Intermediate [A-9] of Synthesis Example 29, except that Intermediate [C-12] was used instead of Intermediate [A-8].

(Synthesis of Intermediate C-14)

A target compound was obtained in the same manner as in Intermediate [A-10] of Synthesis Example 29, except that Intermediate [C-13] was used instead of Intermediate [A-9].

(Synthesis of compound 146)

An organometallic compound 146, a target compound, was obtained in the same manner as in Synthesis Example 29, except that Intermediate [C-14] was used instead of Intermediate [A-10].

(8) Synthesis of organometallic compound 155

N ¹ - (phenyl-di-5), benzene-1,2-diamine instead of ^{N 1 - ([1,1 ':} 3', 1 '' - terphenyl] -2' carbonyl-2,2 '', 3 , 3'', 4,4'', 5,5'', 6,6''-d10) Using the same method as in Synthesis Example 146, except for using benzene-1,2-diamine The compound organometallic compound 155 was obtained.

(9) Synthesis of organometallic compound 167

The same method as in Synthesis Example 155 was followed except that 7-bromo-5H-pyrido [3,2-b] indole was used instead of 7-bromo-5H-pyrido [4,3-b] indole. The target compound, organometallic compound 167, was obtained.

(10) Synthesis of organometallic compound 191

The same method as in Synthesis Example 155 was followed except that 3-bromo-5H-pyrido[4,3-b]indole was used instead of 7-bromo-5H-pyrido[4,3-b]indole. The target compound, organometallic compound 191, was obtained.

¹ H NMR and MS/FAB of the compounds synthesized in the above synthesis example are shown in Table 1 below. Compounds other than those shown in Table 1 can also be easily recognized by those skilled in the art by referring to the above synthetic routes and raw materials.

division ¹ H NMR (CDCl ₃ , 400 MHz) MS/FAB found calc. compound 18 δ 8.87(s, 1H), 8.74(d, 1H), 8.39(m, 2H), 7.43~7.38(m, 5H), 7.12-7.08(m, 2H), 6.71~6.69(m, 3H), 1.32 (s, 9H) 736.2397 736.2396 compound 29 δ 8.87 (s, 1H), 8.73 (d, 1H), 8.42 to 8.39 (m, 2H), 7.41 to 7.38 (m, 3H), 7.14 to 7.12 (m, 3H), 6.95 to 6.94 (m, 2H) , 6.70~6.68(m, 2H), 1.35(s, 9H), 1.32(s, 9H) 999.4086 999.4088 compound 50 δ 8.74(d, 1H), 8.39(d, 1H), 8.10(m, 1H), 7.53(m, 1H), 7.39-7.33(m, 7H), 7.15-7.13(m, 3H), 7.01~6.99 (m, 6H), 6.69(d, 1H), 2.92(s, 6H), 2.89(s, 3H), 2.51(s, 3H), 2.48(s, 3H), 1.32(s, 9H) 1034.4117 1034.4118 compound 79 δ 8.74(d, 1H), 8.42~8.39(m, 2H), 8.10(d, 1H), 7.97(d, 1H), 7.41-7.39(m, 4H), 7.22-7.13(m, 5H), 6.98 ~6.96(m, 2H), 6.70(s, 1H), 6.68(d, 1H), 1.35(s, 9H), 1.33(s, 9H) 931.3556 931.3555 compound 119 δ 8.74(d, 1H), 7.46-7.44(m, 3H), 7.11-7.09(m, 3H), 6.987(d, 1H), 6.51(d, 1H), 1.37(s, 9H), 1.35(s) , 9H), 1.32(s, 9H), 1.30(s, 9H) 954.4402 954.4400 compound 129 δ 8.87(s, 1H), 8.74(d, 1H), 8.46-8.43(m, 2H), 7.46~7.38(m, 4H), 7.23-7.21(m, 2H), 7.01~6.99(m, 4H) , 1.37 (s, 18H), 1.32 (s, 9H) 928.3540 928.3542 compound 146 δ 9.32(s, 1H), 8.74(d, 1H), 8.46(d, 1H), 8.34(d, 1H), 7.51~7.41(m, 5H), 7.14-7.12(m, 2H), 7.05(s) , 1H), 6.95 to 6.94 (m, 2H), 1.41 (s, 9H), 1.33 (s, 9H) 873.2980 873.2979 compound 155 δ 9.34(s, 1H), 8.74(d, 1H), 8.46(d, 1H), 8.35(m, 1H), 8.20(d, 2H), 7.51~7.43(m, 6H), 7.14-7.12(m) , 2H), 7.06 (s, 1H), 6.96 to 6.95 (m, 2H), 1.42 (s, 9H), 1.33 (s, 9H) 1030.3916 1030.3918 compound 167 δ 8.73(d, 1H), 8.46-8.44(m, 2H), 8.20(d, 2H), 7.97(d, 1H), 7.46~7.38(m, 5H), 7.21-7.14(m, 3H), 7.05 (s, 1H), 6.96 to 6.95 (m, 2H), 1.40 (s, 9H), 1.32 (s, 9H) 1030.3917 1030.3918 compound 191 δ 8.74(d, 1H), 8.54(d, 1H), 8.38(s, 1H), 8.20(d, 2H), 7.94(d, 1H), 7.43~7.35(m, 5H), 7.17-7.14(m) , 3H), 7.05 (s, 1H), 6.96 to 6.95 (m, 2H), 1.41 (s, 9H), 1.32 (s, 9H) 1030.3919 1030.3918

2. Characterization of organometallic compounds

Example compounds 18, 29, 50, 79, 119, 129, 146, 155, 167, 191, and Comparative Example compounds C1 to C3 to evaluate the emission characteristics of the organometallic compounds of the compounds are shown in Table 2 below.

Example compounds and comparative example compounds are as follows.

[Example compound]

[Comparative Example Compound]

division T1 (nm) T1 level (eV) ³ MLCT (%) ³ MC (eV) organometallic compound 18 459 2.70 13.4 0.56 organometallic compounds 29 453 2.73 14.6 0.81 organometallic compounds 50 456 2.72 13.3 0.68 organometallic compounds 79 460 2.70 15.0 0.66 organometallic compounds 119 455 2.72 13.2 0.75 organometallic compounds 129 459 2.70 17.4 0.78 organometallic compounds 146 448 2.82 18.5 0.75 organometallic compounds 155 447 2.83 21.0 0.86 organometallic compounds 167 463 2.68 17.5 0.71 organometallic compounds 191 450 2.80 19.4 0.82 Comparative Example Compound C1 467 2.65 11.9 0.54 Comparative Example Compound C2 466 2.65 12.3 0.55 Comparative Example Compound C3 470 2.64 8.8 0.41

Table 2 shows the quantum simulation results of the lowest triplet excitation energy level (T1 level), ³ MLCT (Metal to Ligand Charge Transfer) and ³ MC (3 Metal Centered state) energy for each compound according to the B3LYP DFT calculation method. is shown.

Referring to the results of Table 2, the example compounds, organometallic compounds 18, 29, 50, 79, 119, 129, 146, 155, 167, and 191 were ³ MLCT ( Metal to Ligand Charge Transfer) values, and it can be seen that the organometallic compounds of Examples exhibit a similar level or an increased ³ MC (3 Metal Centered state) value compared to Comparative Examples C1 to C3. Accordingly, when the organometallic compounds of the example are applied to the light emitting device, it can be expected that the device lifespan and the light emitting efficiency characteristics are improved compared to the case where the compounds of the comparative example are applied.

In addition, it can be seen that the organometallic compounds 18, 29, 50, 79, 119, 129, 146, 155, 167 and 191, which are the example compounds, have shorter wavelengths than those of the comparative example compounds C1 to C3. In Comparative Example Compound C1, _{only X 1} of the carboline group is a nitrogen atom, that is, it is determined that a nitrogen atom is included only in the α (alpha) position of the carboline group to exhibit a longer wavelength value than the compounds of Examples. Comparative Example Compound C3 does not include a carboline group, and thus it is determined that it exhibits a longer wavelength value than the Example compounds and Comparative Example Compound C1.

On the other hand, as compared to Comparative Example Compound C1, Example Compound 29 and Compound 119 include a plurality of deuterium atom substituents, ^{it is determined to exhibit a high 3} MC (3 Metal Centered state) value.

3. Fabrication and evaluation of organic electroluminescent devices

(Production of organic electroluminescent device)

The organic electroluminescent device of one embodiment including the organometallic compound of one embodiment in the light emitting layer was prepared by the following method. The organic electroluminescent devices of Examples 1 to 10 were prepared by using the compounds 18, 29, 50, 79, 119, 129, 146, 155, 167 and 191 as described above as dopant materials for the emission layer. In Comparative Examples 1 and 2, organic electroluminescent devices were manufactured by using the above-described Comparative Examples Compounds C1 and C3 as dopant materials for the emission layer.

As a substrate and an anode, Corning's 15Ω/cm ² (1200Å) ITO-formed glass substrate was cut into 50mm x 50mm x 0.7mm and ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, 30 minutes During the period, ultraviolet rays were irradiated and cleaned by exposure to ozone, and the glass substrate was installed in a vacuum deposition apparatus.

2-TNATA was vacuum deposited on the ITO anode formed on the organic substrate to form a hole injection layer having a thickness of 600 Å, and NPB was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.

On the hole transport layer, co-host BCPDS and POPCPA (weight ratio of BCPDS and POPCPA) and dopant Example compounds or comparative example compounds were co-deposited so that the weight ratio of co-host and dopant was 90: 10 to form a light emitting layer with a thickness of 300 Å.

TSPO1 was deposited on the light emitting layer to form a hole blocking layer with a thickness of 50 Å, Alq ₃ was deposited on the hole blocking layer to form an electron transport layer with a thickness of 300 Å, and then LiF was deposited on the electron transport layer to a thickness of 10 Å After forming the electron injection layer of, Al was vacuum-deposited on the electron injection layer to form a cathode with a thickness of 3000 Å, thereby manufacturing an organic electroluminescent device.

division dopant material Driving voltage (V) current density
(mA/cm ² ) luminance
(cd/m ² ) Luminous Efficiency
(cd/A) Maximum emission wavelength (nm) Half life (hr) Example 1 compound 18 4.35 50 3750 11.35 450 125 Example 2 compound 29 4.51 50 3985 13.50 455 175 Example 3 compound 50 4.42 50 4115 14.75 453 157 Example 4 compound 79 4.38 50 3945 13.18 458 128 Example 5 compound 119 4.45 50 4450 16.69 452 186 Example 6 compound 129 4.21 50 4325 15.16 451 102 Example 7 compound 146 4.24 50 4100 14.16 457 83 Example 8 compound 155 4.55 50 4310 16.57 450 117 Example 9 compound 167 4.53 50 4355 15.87 459 115 Example 10 compound 191 4.62 50 4300 16.40 453 106 Comparative Example 1 Comparative Example Compound C1 5.13 50 2110 6.52 461 45 Comparative Example 2 Comparative Example Compound C3 5.08 50 2405 8.45 460 15

Table 3 shows the evaluation results of the organic electroluminescent devices for Examples 1 to 10, Comparative Example 1 and Comparative Example 2. Table 3 compares the driving voltage, luminance, luminous efficiency, emission wavelength, and lifetime of the manufactured organic electroluminescent device. The luminous efficiency represents a current efficiency value for a current density of 50 mA/cm ^{2 .}

Referring to the results in Table 3, it can be seen that the organic electroluminescent devices of Examples 1 to 10 exhibit excellent luminance and luminous efficiency as compared to the organic electroluminescent devices of Comparative Examples 1 and 2. In addition, it can be seen that the organic electroluminescent devices of Examples 1 to 10 have a lower driving voltage and an increased lifespan compared to the organic electroluminescent devices of Comparative Examples 1 and 2 .

In Comparative Example Compound C1, _{only X 1} of the carboline group is a nitrogen atom, that is, it is determined that a nitrogen atom is included only in the α (alpha) position of the carboline group, thereby exhibiting lower luminous efficiency than the compounds of Examples.

The organometallic compound of an exemplary embodiment may include a carboline group and a deuterium atom to exhibit an improved MLCT ratio, and thus may exhibit improved luminous efficiency. In addition, the organic electroluminescent device of an embodiment may include an organometallic compound including a carboline group and a deuterium atom in the light emitting layer to exhibit excellent luminous efficiency and improved lifespan characteristics.

Although the above has been described with reference to the preferred embodiment of the present invention, those skilled in the art or those having ordinary knowledge in the technical field will not depart from the spirit and technical scope of the present invention described in the claims to be described later. It will be understood that various modifications and variations of the present invention can be made without departing from the scope of the present invention.

Accordingly, the technical scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be defined by the claims.

10: organic electroluminescent element EL1: first electrode
EL2: second electrode HTR: hole transport region
EML: light emitting layer ETR: electron transport region

Claims (20)

a first electrode;
a second electrode disposed on the first electrode; and
a light emitting layer disposed between the first electrode and the second electrode; including,
The light emitting layer is an organic electroluminescent device comprising an organometallic compound represented by the following Chemical Formula 1:
[Formula 1]

In Formula 1,
M is a transition metal,
One or two selected from X ₁ to X ₆ is N, the rest is CR ₄ ,
When X ₁ is N, any one of _{X 2} to X _{6 is N,}
R ₄ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
A ₁ to A ₃ are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 1 to 60 carbon atoms,
b1 to b3 are each independently an integer of 1 or more and 4 or less,
R ₁ to R ₃ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, A substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C6-C6 An aryl group of 60 or less, or a substituted or unsubstituted heterocyclic group having 1 or more and 10 or less ring carbon atoms,
At least one of R ₁ to R ₃ is a deuterium atom or CD ₃ , or at least one of _{R 1} to R ₃ is substituted with a _{deuterium atom or CD 3 ,}
L is a direct bond, O, S, —CR ₁₁ R ₁₂ —, —CR ₁₃ =CR ₁₄ —, —C≡C—, —C(=O)—, —C(=S)—, —BR ₁₅ — , —NR ₁₆ —, —PR ₁₇ R ₁₈ —, or —GeR ₁₉ R ₂₀ —,
R ₁₁ to R ₂₀ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. The method of claim 1,
Wherein M is Pt, Pd, Cu, or Os organic electroluminescent device. The method of claim 1,
The light emitting layer is an organic electroluminescent device that emits phosphorescence. The method of claim 1,
The light emitting layer includes a host and a dopant,
The dopant is an organic electroluminescent device comprising an organometallic compound represented by Formula 1. The method of claim 1,
Formula 1 is an organic electroluminescent device represented by Formula 2-1 or Formula 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,
A ₁ to A ₃ , X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b ₃ are the same as defined in Formula 1 above. The method of claim 1,
Formula 1 is an organic electroluminescent device represented by Formula 3 below:
[Formula 3]

In Formula 3,
R ₅₀ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
M, L, X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b ₃ are the same as defined in Formula 1 above. 7. The method of claim 6,
Formula 3 is an organic electroluminescent device represented by the following Formula 3-1:
[Formula 3-1]

In Formula 3-1,
Any one of X ₂ to X ₆ is N, the rest is CR ₄ ,
M, L, R ₁ to R ₄ , R ₅₀ and b ₁ to b ₃ are the same as defined in Formula 3 above. 7. The method of claim 6,
Formula 3 is an organic electroluminescent device represented by Formula 3-2 or Formula 3-3:
[Formula 3-2]

[Formula 3-3]

In Formula 3-2,
Any one of X ₂ to X ₄ is N, the rest is CR ₄ ,
R ₅ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
In Formula 3-3,
Any one of X ₅ and X ₆ is N, the other is CR ₆ ,
b4 is an integer of 1 or more and 4 or less,
R ₆ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
M, L, R ₁ to R ₄ , b ₁ to b ₃ , and R ₅₀ are the same as defined in Formula 3 above. 7. The method of claim 6
Wherein R ₅₀ is an organic electroluminescent device represented by any one of the compounds of the following compound group R:
[Compound group R]

. 10. The method of claim 9,
When R ₅₀ is a compound R-7 or R-8, R ₁ is an organic electroluminescent device comprising at least one deuterium atom. The method of claim 1,
The light emitting layer is an organic electroluminescent device comprising at least one of the compounds shown in the following compound group 1:
[Compound group 1]

. An organometallic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
M is a transition metal,
One or two selected from X ₁ to X ₆ is N, the rest is CR ₄ ,
When X ₁ is N, any one of _{X 2} to X _{6 is N,}
R ₄ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
A ₁ to A ₃ are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 1 to 60 carbon atoms,
b1 to b3 are each independently an integer of 1 or more and 4 or less,
At least one of R ₁ to R ₃ includes a deuterium atom, and the rest are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted An amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, or a substituted or unsubstituted alkyl group having 2 to 60 carbon atoms a nyl group, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 1 to 10 ring carbon atoms,
L is a direct bond, O, S, —CR ₁₁ R ₁₂ —, —CR ₁₃ =CR ₁₄ —, —C≡C—, —C(=O)—, —C(=S)—, —BR ₁₅ — , —NR ₁₆ —, —PR ₁₇ R ₁₈ —, or —GeR ₁₉ R ₂₀ —,
R ₁₁ to R ₂₀ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 13. The method of claim 12,
Wherein M is Pt, Pd, Cu, or Os organometallic compound. 13. The method of claim 12,
Formula 1 is an organic electroluminescent device represented by Formula 2-1 or Formula 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,
A ₁ to A ₃ , X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b ₃ are the same as defined in Formula 1 above. 13. The method of claim 12,
Formula 1 is an organometallic compound represented by Formula 3 below:
[Formula 3]

In the above formula (3)
R ₅₀ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
M, L, X ₁ to X ₆ , R ₁ to R ₃ , and b ₁ to b ₃ are the same as defined in Formula 1 above. 16. The method of claim 15,
Formula 3 is an organometallic compound represented by the following Formula 3-1:
[Formula 3-1]

In the above formula 3-1
Any one of X ₂ to X ₆ is N, the rest is CR ₄ ,
M, L, R ₁ to R ₄ , R ₅₀ and b ₁ to b ₃ are the same as defined in Formula 3 above. 16. The method of claim 15,
Formula 3 is an organometallic compound represented by Formula 3-2 or Formula 3-3:
[Formula 3-2]

[Formula 3-3]

In Formula 3-2,
Any one of X ₂ to X ₄ is N, the rest is CR ₄ ,
In Formula 3-3,
any one of X ₅ and X ₆ is N, the other is CR ₅ ,
b4 is an integer of 1 or more and 4 or less,
R ₅ is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
M, L, R ₁ to R ₄ , b ₁ to b ₃ , and R ₅₀ are the same as defined in Formula 3 above. 16. The method of claim 15,
Wherein R ₅₀ is an organometallic compound represented by any one of the compounds of the following compound group R:
[Compound group R]

. 19. The method of claim 18,
When R ₅₀ is compound R-7 or R-8, R ₁ is an organometallic compound containing at least one deuterium atom. 13. The method of claim 12,
Formula 1 is an organometallic compound represented by any one of the compounds of the following compound group 1:
[Compound group 1]

.

Images